Compounds having multiple primary amine functional groups are used in a wide variety of applications. Polymeric materials such as polyamides, epoxy polymers, polyureas and other polymers can be formed by condensation reactions of amine-functionalized monomers such as diamines, triamines or tetramines with monomers having other functional groups. Polyamides typically are formed by reaction of a diamine monomer such as ethylenediamine or hexamethylenediamine, with a diacid monomer such as adipic acid or with a diacid chloride monomer such as sebacoyl chloride or terephthaloyl chloride. Epoxy polymers typically are formed by reaction of amine-functionalized monomers such as ethylenediamine, triethylenetriamine, diethylenetriamine, hexamethylenetetramine, tetraethylenepentamine, or amine-terminated polymers or prepolymers with monomers having two or more epoxy groups, such as diglycidyl ethers of bisphenol A or bisphenol F, tetraglycidyl diamine-diphenylmethane, or multi-glycidyl ethers of phenol formaldehyde novolac polymers. Polyureas typically are formed by reaction of a diamine or triamine monomer with a diisocyanate monomer.
Compounds having multiple primary amine functional groups also are used to form dendritic molecules. Dendritic molecules may be used as solubility enhancers, as catalyst supports, as immunoassay components, and as precursors for advanced materials. Species of the poly(amido amine) (PAMAM) class of dendrimers typically are formed by alternating reaction of ethylenediamine and methyl acrylate. Examples of PAMAM dendrimers include but are not limited to [NH2(CH2)2NH2]: (G=0);dendri PAMAM(NH2)4 and its associated higher generation molecules.
The physical and chemical properties of polymers and of dendritic molecules are affected by the chemical structures of the building blocks used to prepare the polymers and/or dendritic molecules. Alteration of the chemical structure, size and/or concentration of these building blocks can allow for modification of the properties of the polymer or dendritic molecule.
It is desirable to expand the chemical structures present in compounds having multiple primary amine functional groups, so as to expand the useful properties that can be provided by polymers or dendritic molecules formed from the compounds. With regard to polymers, for example, properties such as flexibility, toughness, etc. can be increased by incorporating chemical groups that lower the modulus or that can absorb energy, respectively. This expansion of chemical structures may be accomplished through post-polymerization processing, such as reaction with other reagents or blending with other polymers. It is especially desirable, however, to expand the chemical structures by introducing new chemical structures in the monomeric building blocks from which the polymer is formed. With regard to dendritic molecules, properties such as solubility, chemical reactivity, density, etc. can be changed by incorporating branches having different chain lengths and substitution points.
One potential approach to altering the chemical structure of compounds having multiple primary amine functional groups is to form the compounds from renewable feedstocks. Renewable feedstocks, such as fatty acids or fatty esters derived from natural oils, have opened new possibilities for the development of a variety of industrially useful substances, including specialty chemicals and intermediates. For example, renewable feedstocks can be used to prepare compounds having combinations of properties that were not available with conventional petroleum feedstocks. In another example, renewable feedstocks can be used to prepare compounds more efficiently, without requiring undesirable reagents or solvents, and/or with decreased amounts of waste or side products.
It would be desirable to provide compounds having multiple primary amine functional groups that include previously unavailable chemical structures. Preferably such compounds can be used as substitutes for conventional amine-functionalized compounds, while providing an increase in the renewable content of the final product formed using the compounds. Preferably such compounds can provide useful combinations of properties that are difficult to obtain using compounds formed from conventional petroleum feedstocks.